3-Amino-1,2-propanediol → HCID 131727153, compound

HRID 269634Notes

Reaction equation

HRID 269634 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH2:34]([O:41][C:42]([NH:44][CH2:45][CH2:46][CH2:47][C@@H:48]([C:57]([OH:59])=O)[NH:49][C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[NH2:60][CH2:61][CH:62]([OH:65])[CH2:63][OH:64]>CN(C=O)C>[CH2:34]([O:41][C:42](=[O:43])[NH:44][CH2:45][CH2:46][CH2:47][C@H:48]([NH:49][C:50]([O:52][C:53]([CH3:54])([CH3:55])[CH3:56])=[O:51])[C:57]([NH:60][CH2:61][CH:62]([OH:65])[CH2:63][OH:64])=[O:59])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 735613-Amino-1,2-propanediolHCID 81531DiisopropylethylamineHCID 7269338(2S)-5-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}pentanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 131727153HCID 131727153, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

658.5 mg (1.8 mmol) of HATU and 129.2 mg (1 mmol) of N,N-diisopropylethylamine are added to a solution of 366 mg (1 mmol) of N5-[(benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-ornithine in 15 ml of anhydrous DMF. After stirring at RT for 15 min, 182.2 mg (1 mmol) of 3-aminopropane-1,2-diol are added. The reaction mixture is stirred at RT for 15 h. The solvent is then evaporated and the residue is taken up in dichloromethane. The organic phase is washed with water, dried over magnesium sulfate and concentrated. The crude product is purified by preparative HPLC.

Workup

  1. stirringThe reaction mixture is stirred at RT for 15 h
  2. customThe solvent is then evaporated
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-2c6c4f0fcbea455eb674d1257da216d2
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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